Hydrochloric Acid → HCID 22339361, compound

HRID 585044Notes

Reaction equation

HRID 585044 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH3:41])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[NH:27][C:28]([C:30]2[CH:38]=[C:37]([Cl:39])[C:36]([Cl:40])=[CH:35][C:31]=2[C:32]([OH:34])=[O:33])=[O:29])=[CH:12][CH:11]=1)=O)(C)(C)C.Cl>CO>[NH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]([CH3:41])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:19][C:18]=2[NH:27][C:28]([C:30]2[CH:38]=[C:37]([Cl:39])[C:36]([Cl:40])=[CH:35][C:31]=2[C:32]([OH:34])=[O:33])=[O:29])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22339365HCID 22339365, compound

Product 1

HCID 22339361HCID 22339361, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a vial is placed 2-({[2-[(4-{[(tert-butoxycarbonyl)amino]methyl}phenyl)(methyl)amino]-5-(trifluoromethyl)phenyl]amino}carbonyl)-4,5-dichlorobenzoic acid (34 mg, 0.056 mmol) and MeOH (5 mL) saturated with HCl. The mixture is stirred at rt for 2 h. The solution is concentrated and the product purified by preparative thin layer chromatography. The yield is 12 mg of 2-({[2-[[4-(aminomethyl)phenyl](methyl)amino]-5-(trifluoromethyl)phenyl]amino}carbonyl)-4,5-dichlorobenzoic acid, 42%. DMSO: 13.3 (s, 1 H), 8.48 (s, 1 H), 7.76 (s, 2 H), 7.51 (m, 1 H), 7.41 (m, 1 H), 7.16 (m, 2 H), 6.60-6.58 (m, 2 H), 3.81 (s, 2 H), 3.22 (s, 3 H). ESI+ for C23H18Cl2F3N3O3 497 (M+H)+.

Workup

  1. concentrationThe solution is concentrated
  2. customthe product purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-1de705ee55f04f6d84938f26532c3146
Source dataset
uspto-grants-2005_08
Patent number
US06930106B2

Reaction notes

Loading…